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Methylamine → 5-((4-fluorophenyl)ethynyl)-N,2-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole-8-carboxamide

HRID 1400629
Notes
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Reaction equation

HRID 1400629 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][N:10]2[C:18]3[CH:17]=[CH:16][C:15]([C:19](O)=[O:20])=[CH:14][C:13]=3[C:12]3[CH2:22][N:23]([CH3:26])[CH2:24][CH2:25][C:11]2=3)=[CH:4][CH:3]=1.C[CH2:28][N:29]=C=NCCCN(C)C.Cl.CN.C1COCC1>CN(C=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]#[C:9][N:10]2[C:18]3[CH:17]=[CH:16][C:15]([C:19]([NH:29][CH3:28])=[O:20])=[CH:14][C:13]=3[C:12]3[CH2:22][N:23]([CH3:26])[CH2:24][CH2:25][C:11]2=3)=[CH:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6329MethylamineHCID 8028TetrahydrofuranHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 594551205-((4-fluorophenyl)ethynyl)-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole-8-carboxylic acid

Product 1

HCID 594551165-((4-fluorophenyl)ethynyl)-N,2-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole-8-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-(4-Fluoro-phenylethynyl)-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole-8-carboxylic acid (20 mg, 0.0044 mmol) was dissolved in DMF and EDCI.HCl (42.17 mg, 0.22 mmol) was added. Methyl amine (2.0 M) in THF (0.0446 mL, 0.0089 mmol) was added. The reaction mixture was stirred at RT overnight. The progress of reaction was monitored by TLC and LCMS. The DMF was evaporated under vacuum and the product purified by HPLC. 1H NMR (CD3OD, TFA salt) δ (ppm): 8.05 (s, 1H), 7.82 (d, 1H), 7.62 (m, 3H), 7.20 (t, 2H), 4.40 (m, 1H), 3.70 (m, 1H), 3.38 (m, 4H), 3.20 (s, 3H), 2.90 (s, 3H).

Workup

  1. customThe progress of reaction
  2. customThe DMF was evaporated under vacuum
  3. customthe product purified by HPLC

Sources & evidence

ORD record
ord-6d6c2a28e5bf441f9ee35424a917c4f6
Source dataset
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08906925B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes